565-69-5Relevant articles and documents
Conversion of Propanal to Pentan-3-one using Lanthanide Oxides
Claridge, John B.,Green, Malcolm L. H.,Tsang, Shik Chi,York, Andrew P. E.
, p. 1089 - 1094 (1993)
The heterogeneous reaction between propanal vapour and rare-earth-metal oxides gives as major products pentan-3-one and carbon dioxide.Residence time investigations indicate that pentan-3-one and carbon dioxide are primary products.Deactivation and high-resolution electron microscopy studies support the hypothesis that surface participates in the reaction, and high oxygen mobilities in the oxide may allow defects to spread within the oxide.The carbon dioxide produced in the reaction poisons the lanthanum oxide leading to the faster deactivation and temperature-programmed desorption indicates the presence of a surface intermediate which decomposes to pentan-3-one and carbon dioxide.A mechanism is proposed in which the formation of pentan-3-one proceeds via surface-bound carboxylate species.Preliminary studies show that catalytic production of pentan-3-one can potentially be sustained by co-feeding water with propanal to the rare-earth-metal oxides.
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Munk
, p. 664 (1905)
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Rational Design of a Metallocatalytic Cavitand for Regioselective Hydration of Specific Alkynes
Endo, Naoki,Inoue, Mami,Iwasawa, Tetsuo
supporting information, p. 1136 - 1140 (2018/03/13)
The synthesis of a functionalized supramolecular cavitand with inwardly oriented AuI and P=O moieties was explored, including its catalytic proclivity in the selective hydration of internal alkynes. The cavitand works as a supramolecular flask device: AuI coordinates to the triple bond, the P=O moiety connects with a H2O molecule, and the cavity favors folding of a single alkynyl side chain. Several tests of different substrate patterns indicated that the cavity was substrate specific, similar to enzymatic catalysis.
Regioselective Isomerization of 2,3-Disubstituted Epoxides to Ketones: An Alternative to the Wacker Oxidation of Internal Alkenes
Lamb, Jessica R.,Mulzer, Michael,Lapointe, Anne M.,Coates, Geoffrey W.
, p. 15049 - 15054 (2015/12/08)
We report an alternative pathway to the Wacker oxidation of internal olefins involving epoxidation of trans-alkenes followed by a mild and highly regioselective isomerization to give the major ketone isomers in 66-98% yield. Preliminary kinetics and isotope labeling studies suggest epoxide ring opening as the turnover limiting step in our proposed mechanism. A similar catalytic system was applied to the kinetic resolution of select trans-epoxides to give synthetically useful selectivity factors of 17-23 for benzyl-substituted substrates.
